This invention relates to certain cyclic amides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides.
The control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
WO 95/01973 discloses certain heterocyclic amides and esters of Formula i as fungicides ##STR2## wherein Ar is substituted aryl or heteroaryl;
R.sup.1 is alkyl or haloalkyl; PA1 R.sup.2 and R.sup.3 are independently, among others, hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkynyl, alkynyloxy, haloallyl, haloalkoxy, haloalkenyl, haloalkynyl, alkoxycarbonyl, or substituted phenyl; PA1 A is --O--; --CH.dbd.CH--; --C.tbd.C--; --CH.sub.2 O--; --OCH.sub.2 --; --CH.sub.2 S(O).sub.n --; --S(O).sub.n CH.sub.2 --; --S(O).sub.n --; --C(R.sup.4).dbd.N--O--; --C(R.sup.4).dbd.N--OCH.sub.2 --; or --NR.sup.6 --; PA1 Z is OR.sup.5 or NR.sup.6 R.sup.7 ; PA1 R.sup.4 is H, alkyl, haloalkyl, cycloalkyl or cyano; PA1 R.sup.5 is alkyl or haloalkyl; PA1 R.sup.6 and R.sup.7 are independently H, alkyl, haloalkyl or alkoxy; and PA1 n is 0, 1 or 2. PA1 A is O; S; N; NR.sup.5 ; or CR.sup.14 ; PA1 G is C or N; provided that when G is C, then A is O, S or NR.sup.5 and the floating double bond is attached to G; and when G is N, then A is N or CR.sup.14 and the floating double bond is attached to A; PA1 W is O; S; NH; N(C.sub.1 -C.sub.6 alkyl); or NO(C.sub.1 -C.sub.6 alkyl); PA1 X is OR.sup.1 ; S(O).sub.m R.sup.1 ; or halogen; PA1 R.sup.1 is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; or C.sub.2 -C.sub.4 alkoxycarbonyl; PA1 R.sup.2 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; C.sub.2 -C.sub.4 alkoxycarbonyl; hydroxy; C.sub.1 -C.sub.2 alkoxy; or acetyloxy; PA1 R.sup.3 and R.sup.4 are each independently halogen; cyano; nitro; hydroxy; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyloxy; C.sub.2 -C.sub.6 alkynyloxy; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; formyl; C.sub.2 -C.sub.6 alkylcarbonyl; C.sub.2 -C.sub.6 alkoxycarbonyl; NH.sub.2 C(O); (C.sub.1 -C.sub.4 alkyl)NHC(O); (C.sub.1 -C.sub.4 alkyl).sub.2 NC(O); Si(R.sup.25).sub.3 ; Ge(R.sup.25).sub.3 ; (R.sup.25).sub.3 Si--C.tbd.C--; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R.sup.8 and optionally substituted with one or more R.sup.10 ; PA1 R.sup.5 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; or C.sub.2 -C.sub.4 alkoxycarbonyl; PA1 Y is --O--; --S(O).sub.n --; --NR.sup.15 --; --C(.dbd.O)--; --CH(OR.sup.15)--; --CHR.sup.6 --; --CHR.sup.6 CHR.sup.6 --; --CR.sup.6 .dbd.CR.sup.6 --; --C.tbd.C--; --CHR.sup.15 O--; --OCHR.sup.15 --; --CHR.sup.15 S(O).sub.n --; --S(O).sub.n CHR.sup.15 --; --CHR.sup.15 O--N.dbd.C(R.sup.7)--; --(R.sup.7)C.dbd.N--OCH(R.sup.15)--; --C(R.sup.7).dbd.N--O--; --O--N.dbd.C(R.sup.7)--; --CHR.sup.15 OC(.dbd.O)N(R.sup.15)--; --CHR.sup.15 OC(.dbd.S)N(R.sup.15)--; --CHR.sup.15 OC(.dbd.O)O--; --CHR.sup.15 OC(.dbd.S)O--; --CHR.sup.15 OC(.dbd.O)S--; --CHR.sup.15 OC(.dbd.S)S--; --CHR.sup.15 SC(.dbd.O)N(R.sup.15)--; --CHR.sup.15 SC(.dbd.S)N(R.sup.15)--; --CHR.sup.15 SC(.dbd.O)O--; --CHR.sup.15 SC(.dbd.S)O--; --CHR.sup.15 SC(.dbd.O)S--; --CHR.sup.15 SC(.dbd.S)S--; --CHR.sup.15 SC(.dbd.NR.sup.15)S--; --CHR.sup.15 N(R.sup.15)C(.dbd.O)N(R.sup.15)--; --CHR.sup.15 O--N(R.sup.15)C(.dbd.O)N(R.sup.15)--; --CHR.sup.15 O--N(R.sup.15)C(.dbd.S)N(R.sup.15)--; --CHR.sup.15 O--N.dbd.C(R.sup.7)NR.sup.15 --; --CHR.sup.15 O--N.dbd.C(R.sup.7)OCH.sub.2 --; --CHR.sup.15 O--N.dbd.C(R.sup.7)--N.dbd.N--; --CHR.sup.15 O--N.dbd.C(R.sup.7)--C(.dbd.O)--; --CHR.sup.15 O--N.dbd.C(R.sup.7)--C(.dbd.N--A.sup.2 --Z.sup.1)--A.sup.1 --; --CHR.sup.15 O--N.dbd.C(R.sup.7)--C(R.sup.7).dbd.N--A.sup.2 --A.sup.3 --; --CHR.sup.15 O--N.dbd.C(--C(R.sup.7).dbd.N--A.sup.2 --Z.sup.1)--; --CHR.sup.15 O--N.dbd.C(R.sup.7)--CH.sub.2 O--; --CHR.sup.15 O--N.dbd.C(R.sup.7)--CH.sub.2 S--; --O--CH.sub.2 CH.sub.2 O--N.dbd.C(R.sup.7)--; --CHR.sup.15 O--C(R.sup.15).dbd.C(R.sup.7)--; --CHR.sup.15 O--C(R.sup.7).dbd.N--; --CHR.sup.15 S--C(R.sup.7).dbd.N--; --C(R.sup.7).dbd.N--NR.sup.15 --; --CH.dbd.N--N.dbd.C(R.sup.7)--; --CHR.sup.15 N(R.sup.15)--N.dbd.C(R.sup.7)--; --CHR.sup.15 N(COCH.sub.3)--N.dbd.C(R.sup.7)--; --OC(.dbd.S)NR.sup.15 C(.dbd.O)--; --CHR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; --CHR.sup.6 CHR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; --CR.sup.6 .dbd.CR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; --C.tbd.C--C(.dbd.W.sup.1)--A.sup.1 --; --N.dbd.CR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; or a direct bond; and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to E and the moiety on the right side of the linkage is bonded to Z; PA1 Z.sup.1 is H or --A.sup.3 --Z; PA1 W.sup.1 is O or S; PA1 A.sup.1 is O; S; NR.sup.15 ; or a direct bond; PA1 A.sup.2 is O; NR.sup.15 ; or a direct bond; PA1 A.sup.3 is --C(.dbd.O)--; --S(O).sub.2 --; or a direct bond; PA1 each R.sup.6 is independently H; 1-2 CH.sub.3 ; C.sub.2 -C.sub.3 alkyl; C.sub.1 -C.sub.3 alkoxy; C.sub.3 -C.sub.6 cycloalkyl; formylarnino; C.sub.2 -C.sub.4 alkylcarbonylamino; C.sub.2 -C.sub.4 alkoxycarbonylamino; NH.sub.2 C(O)NH; (C.sub.1 -C.sub.3 alkyl)NHC(O)NH; (C.sub.1 -C.sub.3 alkyl).sub.2 NC(O)NH; N(C.sub.1 -C.sub.3 alkyl).sub.2 ; piperidinyl; morpholinyl; 1-2 halogen; cyano; or nitro; PA1 each R.sup.7 is independently H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 haloalkylsulfinyl; C.sub.1 -C.sub.6 haloalkylsulfonyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; C.sub.2 -C.sub.4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy; amino; NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; or morpholinyl; PA1 each Z is independently selected from: PA1 each Q is independently selected from the group --CHR.sup.13 --, --NR.sup.13 --, --O--, and --S(O).sub.p --; PA1 R.sup.8 is H; 1-2 halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 alkenyloxy; CO.sub.2 (C.sub.1 -C.sub.6 alkyl); NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; cyano; nitro; SiR.sup.19 R.sup.20 R.sup.21 ; or GeR.sup.19 R.sup.20 R.sup.21 ; PA1 R.sup.9 is H; 1-2 halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkylthio; C.sub.1 -C.sub.6 alkylsulfinyl; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 alkenyloxy; CO.sub.2 (C.sub.1 -C.sub.6 alkyl); NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; --C(R.sup.18).dbd.NOR.sup.17 ; cyano; nitro; SF.sub.5 ; SiR.sup.22 R.sup.23 R.sup.24 ; or GeR.sup.22 R.sup.23 R.sup.24 ; or R.sup.9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ; PA1 each R.sup.10 is independently halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 alkoxy; nitro; or cyano; or PA1 when R.sup.9 and an R.sup.10 are attached to adjacent atoms on Z, R.sup.9 and said adjacently attached R.sup.10 can be taken together as --OCH.sub.2 O-- or --OCH.sub.2 CH.sub.2 O--; each CH.sub.2 group of said taken together R.sup.9 and R.sup.10 optionally substituted with 1-2 halogen; or PA1 when Y and an R.sup.10 are attached to adjacent atoms on Z and Y is --CHR.sup.15 O--N.dbd.C(R.sup.7)--, --O--N.dbd.C(R.sup.7)--, --O--CH.sub.2 CH.sub.2 O--N.dbd.C(R.sup.7)--, --CHR.sup.15 O--C(R.sup.15).dbd.C(R.sup.7)--, --CH.dbd.N--N.dbd.C(R.sup.7)--, --CHR.sup.15 N(R.sup.15)--N.dbd.C(R.sup.7)-- or --CHR.sup.15 N(COCH.sub.3)--N.dbd.C(R.sup.7)--, R.sup.7 and said adjacently attached R.sup.10 can be taken together as --(CH.sub.2).sub.r -J- such that J is attached to Z; PA1 J is --CH.sub.2 --; --CH.sub.2 CH.sub.2 --; --OCH.sub.2 --; --CH.sub.2 O--; --SCH.sub.2 --; --CH.sub.2 S--; --N(R.sup.16)CH.sub.2 --; or --CH.sub.2 N(R.sup.16)--; each CH.sub.2 group of said J optionally substituted with 1 to 2 CH.sub.3 ; PA1 R.sup.11 and R.sup.12 are each independently halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; nitro; cyano; Si(R.sup.25).sub.3 ; or Ge(R.sup.25).sub.3 ; PA1 each R.sup.13 is independently H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano; PA1 R.sup.14 is H; halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; or C.sub.3 -C.sub.6 cycloalkyl; PA1 each R.sup.15 is independently H; C.sub.1 -C.sub.3 alkyl; C.sub.3 -C.sub.6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano; or PA1 when Y is --CHR.sup.15 N(R.sup.15)C(.dbd.O)N(R.sup.15)--, the two R.sup.15 attached to nitrogen atoms on said group can be taken together as --(CH.sub.2).sub.s --; or PA1 when Y is --CHR.sup.15 O--N.dbd.C(R.sup.7)NR.sup.15 --, R.sup.7 and the adjacently attached R.sup.15 can be taken together as --CH.sub.2 --(CH.sub.2).sub.s --; --O--(CH.sub.2).sub.s --; --S--(CH.sub.2).sub.s --; or --N(C.sub.1 -C.sub.3 alkyl)--(CH.sub.2).sub.s --; with the directionality of said linkage defined such that the moiety depicted on the left side of the linkage is bonded to the carbon and the moiety on the right side of the linkage is bonded to the nitrogen; PA1 R.sup.16, R.sup.17, and R.sup.18 are each independently H; C.sub.1 -C.sub.3 alkyl; C.sub.3 -C.sub.6 cycloalkyl; or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano; PA1 R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 are each independently C.sub.1 -C.sub.6 alkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.4 alkoxy; or phenyl; PA1 each R.sup.25 is independently C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.2 -C.sub.4 alkenyl; C.sub.1 -C.sub.4 alkoxy; or phenyl; PA1 m, n and p are each independently 0, 1 or 2; PA1 r is 0 or 1; and PA1 s is 2 or 3. PA1 E is selected from the group 1H-pyrrole-1,2-, 2,3- and 3,4-diyl; 2,3- and 3,4-furandiyl; 2,3- and 3,4-thiophenediyl; 1H-pyrazole-1,5-, 3,4- and 4,5-diyl; 1H-imidazole-1,2-, 4,5- and 1,5-diyl; 3,4- and 4,5-isoxazolediyl; 4,5-oxazolediyl; 3,4- and 4,5-isothiazolediyl; 4,5-thiazolediyl; 1H-1,2,3-triazole-1,5- and 4,5-diyl; 2H-1,2,3-triazole-4,5-diyl; 1H-1,2,4-triazole-1,5-diyl; 4H-1,2,4-triazole-3,4-diyl; 1,2,3-oxadiazole-4,5-diyl; 1,2,5-oxadiazole-3,4-diyl; 1,2,3-thiadiazole-4,5-diyl; 1,2,5-thiadiazole-3,4-diyl; 1H-tetrazole-1,5-diyl; 2,3- and 3,4-pyridinediyl; 3,4- and 4,5-pyridazinediyl; 4,5-pyrimidinediyl; 2,3-pyrazinediyl; 1,2,3-triazine-4,5-diyl; 1,2,4-triazine-5,6-diyl; 1H-indole-1,4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 1,2-, 2,3-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl; benzo[b]thiophene-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 4,5-, 5,6- and 6,7-diyl; 1H-indazole-1,4-, 1,5-, 1,6-, 1,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; 1H-benzimidazole-1,4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-diyl; 1,2-benzisoxazole-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-benzoxazolediyl; 1,2-benzisothiazole-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-benzothiazolediyl; 2,5-, 2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 2,3-, 3,4-, 5,6-, 6,7- and 7,8-quinolinediyl; 1,5-, 1,6-, 1,7-, 1,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 3,4-, 5,6-, 6,7- and 7,8-isoquinolinediyl; 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 3,4-, 5,6-, 6,7- and 7,8-cinnolinediyl; 1,5-, 1,6-, 1,7-, 1,8-, 5,6-, 6,7- and 7,8-phthalazinediyl; 2,5-, 2,6-, 2,7-, 2,8-, 4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-quinazolinediyl; 2,5-, 2,6-, 2,7-, 2,8-, 2,3-, 5,6-, 6,7- and 7,8-quinoxalinediyl; 1,8,-naphthyridine-2,5-, 2,6-, 2,7-, 3,5-, 3,6-, 4,5-, 2,3- and 3,4-diyl; 2,6-, 2,7-, 4,6-, 4,7-, 6,7-pteridinediyl; pyrazolo[5,1-b]thiazole-2,6-, 2,7-, 3,6-, 3,7-, 2,3- and 6,7-diyl; thiazolo[2,3-c]-1,2,4-triazole-2,5-, 2,6-, 5,6-diyl; 2-oxo-1,3-benzodioxole-4,5- and 5,6-diyl; 1,3-dioxo-1H-isoindole-2,4-, 2,5-, 4,5- and 5,6-diyl; 2-oxo-2H-1-benzopyran-3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-diyl; [1,2,4]triazolo[1,5-a]pyridine-2,5-, 2,6-, 2,7-, 2,8-, 5,6-, 6,7- and 7,8-diyl; 3,4-dihydro-2,4-dioxo-2H-1,3-benzoxazine-3,5-, 3,6-, 3,7-, 3,8-, 5,6-, 6,7- and 7,8-diyl; 2,3-dihydro-2-oxo-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-benzofurandiyl; thieno[3,2-d]thiazole-2,5-, 2,6-, and 5,6-diyl; 5,6,7,8-tetrahydro-2,5-, 2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 2,3- and 3,4quinolinediyl; 2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazole-2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-diyl; 1,3-benzodioxole-2,4-, 2,5-, 4,5- and 5,6-diyl; 2,3-dihydro-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-benzofurandiyl; 2,3-dihydro-1,4-benzodioxin-2,5-, 2,6-, 2,7-, 2,8-, 5,6- and 6,7-diyl; 5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2,4-, 2,5-, 2,6-, 2,7-, 2,8-, 3,4-, 3,5-, 3,6-, 3,7-, 3,8-, and 2,3-diyl; and 1,5-, 1,6-, 1,7-, 1,8-, 2,6-, 2,7-, 1,2-, and 2,3-naphthalenediyl; each aromatic ring system optionally substituted with one of R.sup.3, R.sup.4, or both R.sup.3 and R.sup.4 ; PA1 W is O; PA1 R.sup.1 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; PA1 R.sup.2 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; or C.sub.3 -C.sub.6 cycloalkyl; PA1 R.sup.3 and R.sup.4 are each independently halogen; cyano; nitro; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.2 -C.sub.6 alkylcarbonyl; C.sub.2 -C.sub.6 alkoxycarbonyl; (C.sub.1 -C.sub.4 alkyl)NHC(O); (C.sub.1 -C.sub.4 alkyl).sub.2 NC(O); benzoyl; or phenylsulfonyl; PA1 Y is --O--; --CH.dbd.CH--; --C.tbd.C--; --CH.sub.2 O--; --OCH.sub.2 --; --CH.sub.2 S(O).sub.n --; --CH.sub.2 O--N.dbd.C(R.sup.7)--; --(R.sup.7)C.dbd.N--OCH(R.sup.15)--; --C(R.sup.7).dbd.N--O--; --CH.sub.2 OC(O)NH--; --CH.sub.2 S--C(R.sup.7).dbd.N--; --CH.dbd.CR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; or a direct bond; PA1 R.sup.7 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 alkylthio; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.3 -C.sub.6 cycloalkyl; halogen; or cyano; or PA1 when Y and an R.sup.10 are attached to adjacent atoms on Z and Y is --CH.sub.2 O--N.dbd.C(R.sup.7)--, R.sup.7 and said adjacently attached R.sup.10 can be taken together as --(CH.sub.2).sub.r -J- such that J is attached to Z; PA1 Z is selected from the group C.sub.1 -C.sub.10 alkyl; C.sub.3 -C.sub.8 cycloalkyl; phenyl; naphthalenyl; anthracenyl; phenanthrenyl; 1H-pyrrolyl; furanyl; thienyl; 1H-pyrazolyl; 1H-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl; 1H-1,2,3-triazolyl; 2H-1,2,3-triazolyl; 1H-1,2,4-triazolyl; 4H-1,2,4-triazolyl; 1,2,3-oxadiazolyl; 1,2,4-oxadiazolyl; 1,2,5-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,3-thiadiazolyl; 1,2,4-thiadiazolyl; 1,2,5-thiadiazolyl; 1,3,4-thiadiazolyl; 1H-tetrazolyl; 2H-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl; pyrazinyl; 1,3,5-triazinyl; 1,2,4-triazinyl; 1,2,4,5-tetrazinyl; 1H-indolyl; benzofuranyl; benzo[b]thiophenyl; 1H-indazolyl; 1H-benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl; isoquinolinyl; cinnolinyl; phthalazinyl; quinazolinyl; quinoxalinyl; 1,8-naphthyridinyl; pteridinyl; 2,3-dihydro-1H-indenyl; 1,2,3,4-tetrahydronaphthalenyl; 6,7,8,9-tetrahydro-5H-benzocycloheptenyl; 5,6,7,8,9,10-hexahydrobenzocyclooctenyl; 2,3-dihydro-3-oxobenzofuranyl; 1,3-dihydro-1-oxoisobenzofiranyl; 2,3-dihydro-2-oxobenzofuranyl; 3,4-dihydro-4-oxo-2H-1-benzopyranyl; 3,4-dihydro-1-oxo-1H-2-benzopyranyl; 3,4dihydro-3-oxo-1H-2-benzopyranyl; 3,4-dihydro-2-oxo-2H-1-benzopyranyl; 4-oxo-4H-1-benzopyranyl; 2-oxo-2H-1-benzopyranyl; 2,3,4,5-tetrahydro-5-oxo-1-benzoxepinyl; 2,3,4,5-tetrahydro-2-oxo-1-benzoxepinyl; 2,3-dihydro-1,3-dioxo-1H-isoindolyl; 1,2,3,4-tetrahydro-1,3dioxoisoquinolinyl; 3,4-dhydro-2,4-dioxo-2H-1,3-benzoxazinyl; 2-oxo-1,3-benzodioxyl; 2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazolyl; 9H-fluorenyl; azulenyl; and thiazolo[2,3-c]-1,2,4-triazolyl; each group substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ; PA1 R.sup.9 is H; 1-2 halogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; C.sub.1 -C.sub.6 alkylthio; cyano; CO.sub.2 (C.sub.1 -C.sub.6 alkyl); NH(C.sub.1 -C.sub.6 alkyl); N(C.sub.1 -C.sub.6 alkyl).sub.2 ; SiR.sup.22 R.sup.23 R.sup.24 ; or GeR.sup.22 R.sup.23 R.sup.24 ; or R.sup.9 is C.sub.3 -C.sub.6 cycloalkyl, phenyl, phenoxy, pyridinyl, pyridinyloxy, pyrimidinyl, or pyrinidinyloxy, each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ; and PA1 each R.sup.15 is independently H; C.sub.1 -C.sub.3 alkyl; or C.sub.3 -C.sub.6 cycloalkyl. PA1 E is selected from the group 2,3- and 3,4-furandiyl; 2,3- and 3,4-thiophenediyl; 2,3- and 3,4-pyridinediyl; 4,5-pyrimidinediyl; 2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl; benzo[b]thiophene-2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-diyl; and 1,6-, 1,7-, 1,2-, and 2,3-naphthalenediyl; each aromatic ring system optionally substituted with one of R.sup.3, R.sup.4, or both R.sup.3 and R.sup.4 ; PA1 Z is selected from the group phenyl; 1,2,4-thiadiazolyl; pyridinyl; pyrimidinyl; and naphthalenyl; each group substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ; PA1 R.sup.7 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 alkylthio; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; cyclopropyl; halogen; or cyano; or when Y and an R.sup.10 are attached to adjacent atoms on Z and Y is --CH.sub.2 O--N.dbd.C(R.sup.7)--, R.sup.7 and said adjacently attached R.sup.10 can be taken together as --(CH.sub.2).sub.r -J- such that J is attached to Z; PA1 J is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --; and PA1 r is 1. PA1 A is O; N; NR.sup.5 ; or CR.sup.14 ; PA1 X is OR.sup.1 ; PA1 R.sup.1 is C.sub.1 -C.sub.3 alkyl; PA1 R.sup.2 is H or C.sub.1 -C.sub.2 alkyl; PA1 Y is --O--; --CH.dbd.CH--; --CH.sub.2 O--; --CH.sub.2 O--N.dbd.C(R.sup.7)--; --(R.sup.7)C.dbd.N--OCH(R.sup.15)--; --CH.sub.2 OC(.dbd.O)NH--; --CH.sub.2 S--C(R.sup.7).dbd.N--; or --CH.dbd.CR.sup.6 --C(.dbd.W.sup.1)--A.sup.1 --; PA1 R.sup.7 is H; C.sub.1 -C.sub.3 alkyl; C.sub.1 -C.sub.3 haloalkyl; C.sub.1 -C.sub.3 alkoxy; C.sub.1 -C.sub.3 alkylthio; or cyclopropyl; and PA1 each R.sup.15 is independently H; C.sub.1 -C.sub.3 alkyl; or cyclopropyl. PA1 A is O or NR.sup.5 ; PA1 G is C; and PA1 Y is --O--; --CH.sub.2 O--; or --CH.sub.2 O--N.dbd.C(.sup.7)--. PA1 R.sup.1 is methyl; and PA1 R.sup.2 is methyl. PA1 A is N or CR.sup.14 ; PA1 G is N; and PA1 Y is --O--; --CH.sub.2 O--; or --CH.sub.2 O--N.dbd.CR.sup.7)--. PA1 R.sup.1 is methyl; and PA1 R.sup.2 is methyl. PA1 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-(trimethylsilyl)phenyl]ethylid ene]amino]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one; PA1 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[ 1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]-3-thienyl]-3H-1, 2,4-triazol-3-one; PA1 4-[2-[(2,5-dimethylphenoxy)methyl]-3-thienyl]-2,4-dihydro-5-methoxy-2-methy l-3H-1,2,4-triazol-3-one; PA1 (1,1-dimethylethyl) 2-chloro-3-[3-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl) -2-thienyl]-2-propenoate; PA1 4-[2-[[[3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl]oxy]methyl]-3-thienyl]-2,4 -dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one; and PA1 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[3-[4-(trifluoromethyl)phenyl]-1,2,4- thiadiazol-5-yl]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one.
The cyclic amides of the present invention are not disclosed therein.
J. Heterocyclic Chem., (1987), 24, 465, J. Heterocyclic Chem., (1988), 25, 1307, and Australian J. Chem., (1977), 30 (8), 1815 disclose 4-nitrophenyl isoxazoles (ii), phenyl pyrazolones (iii), and aryl isothiazolinones (iv) respectively. ##STR3##
However, no utility as fungicides is alleged and the cyclic amides of the present invention are not disclosed therein.